Chronicles of an Unexpected Entrepreneur

I never thought I’d do my own thing — oops?  

A few years ago, I sat through an entrepreneurship course with one thought stuck in my mind:

“I’ve already read all these assigned books, and I love the security of working for someone else, so why am I taking this course?”

I pushed the course away, but the course embraced me with open arms. Despite the fact that I didn’t think the course applied to me, the course won me over. I began showing up early and staying late. I even — gasp! — raised my hand to participate.

In hindsight, it makes sense that I had already read the assigned books. I had read them because I enjoyed the topic, but I hadn’t yet come to terms with that.

At the end of it all, two unexpected things happened:

  1. I received the highest mark in the course.
  2. A few months later, I became an entrepreneur.

The irony.


A year and a half ago, I received a tweet from an online friend that linked to a conference about “dominating the world.” I went to that. It blew my mind.

Then, about a year after that, I received a tweet from another online friend that linked to a conference about “misfits living intentionally.” I went to that, too. It also blew my mind.

I had never heard of these conferences before. I didn’t know who was going or what I would learn. I didn’t know how I’d afford the trips — both of them were a few flights away from my hometown of Managua, Nicaragua.

I’m not sure why I bought my tickets within seconds of receiving the tweets, but I’m glad I did.


In the book The Happiness Hypothesis, Jonathan Haidt explains:

“Our emotional side is an Elephant and our rational side is its Rider. Perched atop the Elephant, the Rider holds the reins and seems to be the leader. But the Rider’s control is precarious because the Rider is so small relative to the Elephant. Anytime the six-ton Elephant and Rider disagree about which direction to go, the Rider is going to lose.”

There’s a visceral gut instinct that propels us toward rare opportunities. We’re pulled at them for reasons we can’t explain. Like love at first sight, we’re scared but strangely enthusiastic.

Most people would advise against impulsive habits. Most people would linger over any investment of thousands of dollars.

There are many paths to growth, but only a few will feel right to each of us. Growth is about finding that rightness.

Impulsive or not, I didn’t linger. I bought tickets to those conferences instantly because I felt that surrounding myself with people who get me and get what I’m striving for is my path.


In my few years as an entrepreneur, I’ve found there’s a deep fear in connection.

I work with clients, and so do you. No matter your line of work, you’ve got stakeholders — and those stakeholders are real people. In my own life, I can identify all sorts “clients” I aim to please:

  1. Companies: I sell them websites and consulting.
  2. Readers: I write them blog posts and books.
  3. Family and friends: I spend time and effort maintaining our connections.
  4. Team members: I manage tasks and inspire them to solve problems.

All of these groups are my “clients.” My job is to keep them as happy as possible. It’s tiring and draining, but there’s an alternative…

Instead of fearing connection and focusing on keeping people happy, why not bring your true self to the table?

Bringing my true self to the table means owning up to the fact that I’m not perfect, that I can’t please others without taking care of myself first, that I sometimes do fail.

It’s hard to do this, and I don’t get it right all the time. I clam up and keep my fake smile plastered on when clients push me past my limits. I overcommit to coffee dates when I’m drowning in deadlines. I publish blog posts without proper thought and editing.

Opportunities gust right by me, leaving me cold and wanting.

Sometimes, though, I beat the fear. I look it right in the eyes and dare it to come any closer — but it never does. Once I challenge it, fear doesn’t go away, but it doesn’t get any closer, either.

Despite fearing their reaction, I tell my clients the truth.

Of all the insights I’ve gleaned from my impulsive conference habit, this new one now makes all the sense in the world:

The only speakers I’ve truly enjoyed are the ones that gave the audience their true selves.

They gave us stories, pitfalls, tears, and fears. The speakers I could’ve done without stayed safely inside their shells.

Instead of just the hopeful start and the exuberant end, I want to experience the grueling middle part, too. I want to hear the whole truth about the people around me, on and off the stage. Now I see that everyone around me wants the whole truth, as well.

Your gut instinct doesn’t always makes sense at first — not to you or the people around you — but you never know what new doors it may open.